Managing Up!
Why the Best Technical People Understand More Than Technology
Ep 16

Being technically right is important. But as you move from technician to senior engineer, team lead, or manager, the harder skill is learning how to make technical decisions that also work for the people using the systems.

In this episode, Chris Long and Michael Riggs join Dean to talk about what that looks like inside an MSP: understanding the end-user experience, balancing technical correctness with business priorities, and knowing when the “best” technical answer may not be the best operational decision. They’ll also dig into how AI is changing the expectations placed on technical professionals and why context, judgment, and communication are becoming more valuable as more of the technical work becomes automated.

Building on Soft Skills for Jerks, this conversation goes beyond support communication and into the decisions behind the work.